This May End Badly

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A male whore teaches his client about sin.
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EStaccato
EStaccato
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Lamplight caresses her neck, and I can see her pulse flickering beneath her skin. Her too-cool façade isn't fooling anyone, least of all me. The snap of her movements, the tremble in the wine glass, the slightest warble in her voice, they all betray her.

I place my nearly full glass of burgundy on the end-table, remove my shiny black shoes and socks, and place them neatly to the side of the couch. Her dress swishes about her knees as perpetually shifts her stance, pretending that she's not watching me.

I shrug off my jacket and loosen my tie. "Take off your panties," I tell her.

She grins. "Make me."

My brow furrows, and I step close, towering over her. Then I bend so that my mouth hovers near her ear. The heat of her body crosses the tiny gap to my lips. I inhale, deep and slow. She is so much peppermint and sugar, but I can smell her personal fragrance underneath.

My whisper is crisp. "Behavior comes with rewards. Disappoint me at your own risk."

Unable to turn her head given my proximity, her side-eye takes on the narrowness of calculation. After a moment, she nods.

"Let's test your resolve. Do not breathe until I let go." I snatch the lobe of her ear between my teeth. I can bite hard if I wish, but I hold her and allow the moisture of my breath to collect on her skin. It's a simple instruction, yet my heart beats faster. She stands rigid, her breath still, her only motion the merest twitch of her jaw, and the now thundered flicker of the pulse in her neck. In short order, I release my grip.

Her breasts rise beneath her sun-yellow dress as her lungs fill with air.

"Take off your panties."

Her tongue wets her lips, her nostrils flaring.

She settles her empty wine glass on the bar steamer. Lifting the hem of her dress, she hooks white lacy panties with her thumbs, and drags them downward.

She's slow about it. The fabric, all show and no function, scrapes over her prominent mound, past her tightly trimmed bush, and down her thighs.

"You want me to admire your choice of lingerie? Maybe you're proud of your tidy little pussy and you want me to stare."

The devil's shadow of a smile bends the corner of her mouth.

"Vanity is a sin."

"Is it?"

Grabbing a chair from the nearby table, I have a seat. "Bend over my lap."

She bites her lip. I can see her brain fighting her natural impulse to resist.

I glare. "Did I mention that I'm impatient?"

Stepping forward, she hikes up her dress, and her breasts press upon the crease of my navy suit pants.

I grab a handful of her dark hair and give it a tug. She yelps, her neck and back arched to ease the strain as I hold her immobile.

"For your vanity, two spankings. Choose how you want to receive them, and if I don't like your answer, there will be more spankings."

"What if I want more?"

"You'll receive your discipline as I see fit. Don't make me repeat myself."

She's breathing harder now. I'd like to think she's excited, but misinterpretation of any of her signals means we're done. And I don't want to be done. I want her. And I haven't wanted someone so much in a long time. But if I let her know, the spell is ruined.

She says, "Uh, I guess, one on each cheek."

"You guess?"

"One on each cheek. Please." There's a smile in that 'please'. We'll see how long that smile lasts.

"How hard?"

"As hard as you want."

"How. Hard."

"Um..." She swallows now. "A handprint on each."

CRACK! CRACK!

"Ow... fuuuuuck," she moans.

"Hold still. Spread your legs."

Awkward as she must feel bent over my lap, she parts her legs. I can see the dark ring of her anus, and the hairy base of her vulva.

My body wants to betray me, my erection growing against my pants and into her torso. The animal within begs to slip my fingers into her damp twat. I long to fill my nostrils with her scent, flood my tongue with her unique flavor.

I allow my palm to move firmly over her ass cheeks, watch her anus flex as I place pressure on the reddening marks left over from discipline. My fingers splay, a fraction of an inch from her dirty pucker, and I run them along either side of her beautiful, furry mound...

Then I withdraw.

As I stand, she seems surprised that I lift her and set her on her feet in a fluid motion.

"Get my bag," I say, pointing at the duffle on the dining room table. "Bring it here."

I take position next to a yoga mat that I clocked the moment I walked in. She has hardwood floors, and she's new to the pleasure-pain aspects of my work, so the mat is going to be the perfect place to work. My introductory package, to see if she likes it. That was the agreement.

"Do I look like a bellhop, to you?" she asks, her eyes flashing.

"Insolence has a price."

"I'm counting on it." She wiggles her hips as she fetches my duffle anyway. Her dress sways. I unbutton my top buttons.

She places the straps of the duffle into my hand, her fingertips dragging across my wrist, fingernails chewed short. As I wet my lower lip, she watches my tongue, her eyes narrow, glued to my mouth. I don't hate it.

This chemistry is rare for me. I hope she feels it, too, but I dare not behave as if she does. I have a responsibility to her, to our agreement. That must remain the priority.

Dropping the bag to the floor, I walk around her. She begins to twist, but two firm fingers on her shoulder blade return her to her original posture. "Very good," I say. "Ballroom dancer?"

"I've had a few lessons."

Behind her now, I say, "Lift your skirt."

She does so.

I crack her on the ass once more, and she gasps. This time my hand comes away stinging. "You're a bellhop if I say you are."

"You fucker," she chuckles.

I crack her again, and she hops from foot to foot, hissing.

Reaching around her, I park my hand on her throat and pull her slowly backward into my chest. "Want to make it three?"

"No..." she says, tightly. "Not yet."

She can't see my grin as I release her neck, and I step back. "Take off your dress. Ah-ah. Don't turn around."

Looking at me over her shoulder, she lifts the black straps, and they slide down her arms. The lines of her shoulder blades sharpen as she returns to standing. She does not seem ashamed of her nudity, but I can see her worrying her lip through the mirror upon the mantle.

"Bend over and part your legs," I say. "I want to see properly what I'm working with."

Her presentation does not disappoint. Her ass cheeks have parted once again to reveal her tight, dark hole and the cleft of her pussy. I can see how wet she is now, and I once again rub my hand over her ass cheeks, over the angry cherry marks I've made.

"Do you like what you see?" she asks.

"Kneel down." I guide her into position. "Legs spread. Wider."

As I take a knee, I can smell her cunt immediately. I struggle to banish thoughts of sliding beneath her and asking her to sit while I taste every inch of her fragrant snatch. My cock strains painfully against my pants. But she can't see the tiny wet bloom to the side of my zipper. Her eyes follow my face as I remove the spreader bar from my bag and extend it. After that, I extract a roll of blue silk ribbon. This I use to lash her knees and ankles to either side of the bar.

Her hands, I pull behind her, criss crossing ribbon from her elbows down to her wrists to ensure she is both comfortable and completely unable to wriggle free. Then her wrists are lashed together, and the tails wrapped around the bar as well.

"Can you move?"

"What if I have to pee?" she asks.

"You should have thought of that before we started," I say.

I kneel and lean my open collar close to her nose as I tie her dark hair into a messy bun.

She's painful to look at, my body screaming for her, begging me to explore her every hill and valley, her forests and dark forbidding places. As I stand back and admire the beautiful blue, silk shimmer against her skin, she finally lowers her gaze to my crotch.

She hums. "I didn't think you were attracted to me."

"What the fuck would make you think that?"

"I'm not very beautiful."

My brows drop, pressure forming between my eyes. The words are a growl in my throat. "Lie to me again, and I'm leaving. Do you understand?"

Her coy smile falters, and she swallows visibly.

She whispers, "Yes."

"Don't move," I say. "Do not flinch. Not a muscle."

Leaning forward, I allow my parted lips to drag over hers. Soft, supple, catching where our moisture mingles. And I pull away. It's all I'll allow myself. It's already too much.

She draws shuddering breath, as I stand, and I cannot tear my eyes from hers. Her gaze, soft and focused, remains locked to mine. I fight to look away.

From my bag, I retrieve my next set of tools, and I breathe to center myself.

I place the tiny rubber ring around the collar of the small manual pump, and I place the pump on her already erect nipple. I cannot look at her face or those lips I'm desperate to kiss as I squeeze the bulb and draw her pink length into the tube. She moans softly.

Counting mentally to thirty, the only sound is our breathing. I slide the rubber ring forward and remove the pump. Her rigid, rosy nipple bulges, the black rubber choking it at the base.

I repeat the preparation and suction on the opposite nipple. I begin my count.

"Look at me," she says.

My cheeks flush, but I continue staring toward her navel.

"Why won't you look at me?"

From my bag, I grab the riding crop and whip it against her inner thigh. She yelps. I whip the opposite thigh and then again, the first. Her body quakes with aftershocks, her voice reduced to a trembling moan.

"Speak out of turn again, and I will whip something more sensitive."

I'm somewhat rougher with the pump removal this time, but she doesn't seem to mind. Two thick, stout nipples point straight at me. And a glance at her flared pussy tells me could take my cock quickly and easily. But that's not on the menu tonight.

I climb to my feet and walk around her, studying my work. She sits patiently as I step to the bar steamer and pick up her phone. "What's your code?"

"Why do you want to know?"

I squat in front of her. "I could just hold this to your face, and it will open," I say. "But I haven't done that. Tell me your code."

For a moment, her brow furrows. And then she tells me. I stand, punch in the code, and navigate to her camera app. Then I proceed to walk around her and snap photo after photo.

"You're not..." she starts. Then she says, "What are you going to do with those?"

"They're yours. And if you want to send them to me when we're through, that's your choice. Or if you want to send them to someone else, they'd really spark a conversation, don't you think?"

Turning the screen, I show her the last photo I took.

"Tell me that's not beautiful," I say. When I finally get a ghost of a smile from her, I lower the phone and take one more of her open pussy and exposed anus. "You know, just in case you do send them to me."

"Would you look at them often?" she asks.

"Tell me," I say, unbuttoning my shirt the rest of the way and tossing it onto my coat. "When you are alone, how often do you masturbate your anus?"

"We've talked about this, haven't we?"

"I find people are more... honest at this stage. So, tell me again. How often do you masturbate your anus?"

"...Most of the time."

"That's not what you told me before."

"I'm feeling honest."

"Tell me why you play with your asshole."

"It... makes me hot."

"Yes, but why?"

"I don't know. It's dirty?"

"Dirty gross or dirty taboo?"

"Taboo, probably. It's naughty. And I like the way it feels."

Unbuckling my belt, I ask, "Do you cum from anal stimulation?"

"I haven't." She sighs. "But I want to."

I unbutton my pants and unzip my fly and my cock springs forth, free of its wool prison. Her eyes track accordingly, and her hips shift in response.

My pants fall, and I step out of them. Precum wells up from within my cock, and I swipe it from the head with a fingertip. I run the bead of my viscous fluid across her lips. She closes her eyes, and another ghost of a moan escapes her throat as she licks.

"Do you like my flavor?" I ask.

She whispers. "Yes."

"Shall I try yours?"

"Mmmmm," she hums, her head rolling back.

"You would like that wouldn't you?" I chuckle at her slackened jaw. But I smile. "I suppose you've behaved for a moment or two at least."

I lean her onto her back, her arms pinned beneath. Tied as she is, legs pulled wide to either side, she's helpless. Then I drop onto my knees and place my head on her thigh. She smells glorious. The odor of her arousal is vibrant, potent. But I take my time, gliding my nose along the skin of her inner thigh toward her sex. I can hear her breathing harder as I inhale fully. When I place my nose against her bush and draw that heady aroma into my nose, my cock fucking aches, and I can feel a fresh bead of precum well up from within.

"Fuck, you smell strong," I say, trying to keep the wavering out of my voice. Her only response is a heavy exhale.

I drag my nose downward across her turgid clit, and she whimpers. With my nose poking into the wetness of her vagina, I extend my tongue between her ass cheeks, sliding plenty of spit across her anus as I flick it and savor feeling her little puckered ridges. This time she moans out loud. And then, I lick upward and plunge my tongue deep into her sour, delicious twat.

"Ohhhh fuuuuuuuck," she breathes.

Perhaps I underestimated how turned-on she is, but with my heart threatening to beat out of my chest, I wonder if she's feeling half of what I am. I mush my lips in and around her box and have to tear myself away. Fuck.

Fuck!

Why? What is it about her that I crave so badly?

Climbing over her, I let the slick head of my cock press against her asshole as I kiss her chin and then her mouth. She licks my lips and sucks on them with abandon.

"Do you like the way your pussy smells?"

"Yes."

"Do you like the way you taste?" I ask, hovering over her.

"Are you going to fuck me now?" she says, attempting to rock her hips. "Are you gonna' fill up my ass?" I can't quite believe it when I feel her anus flare, spread just slightly over the head of my cock.

I pull back and flick her nipple. "Naughty. No cutting in line."

She doesn't have time to pout. My mouth finds hers again as I grab and pinch both of her nipples. Tongues warring, we breathe hard as we drink one another, and her kiss-muffled moan is as much whine as it is pleasure.

"Tell me what you want."

"Whatever gets you off. Make me your fuck doll. Use me."

"Tell me what you want."

She hesitates.

"I want your cum inside me."

"Where?"

"Everywhere."

"Be specific," I say, slapping her tits playfully.

"I want to feel your hard cock on my tongue. Fuck my mouth and pump your hot spunk down my throat."

"You like drinking cum?"

"I fucking hate it. But I - I want yours. I want to feel it shoot into my mouth. Is that weird? To want something I hate so much?"

I don't have the presence of mind to respond properly as I lift her up to a kneeling position and shove my cock into her open mouth. I tangle my fingers loosely in her dark hair and try to keep from thrusting. Her head bobs with enthusiasm. As her tongue undulates along the underside of my rod, I marvel that I could feel such all-encompassing sensation without the use of her hands. How the hell did she learn to do this?

I've taken a pill, of course. I'll stay fully erect for an hour at least, and I'll be able to cum a few times, but I don't want to blow that first, powerful load in her mouth. If she can't handle it, that could ruin everything. It wouldn't be the first time. I MUST maintain control, of her and especially myself.

When I pull out, I look at the mess of her saliva dripping down her chin, a glossy trail oozing between her tits and onto her belly.

"Cum in my mouth," she begs, breathing hard. "Please cum in my mouth."

I grab her chin and squeeze. "We have more important work to do."

I've waited long enough for this.

I tip her once more onto her back, her pussy elevated as she lays atop her arms and hands. Dropping between her legs, I find the stream of lady lube running down her ass cheek and I lap it up to her cunt. Her entire body quivers as I latch my mouth onto her clit.

As I flick and suck and swirl my tongue around her sensitive nub and down along her smallest hole, I'm warily thrilled.

x x x

She wasn't terribly nervous in our initial interview, yet she continuously steered around talk of cunnilingus, which is a behavior I find common in less experienced women or women that have experienced unplanned humiliation.

I asked her openly, "Why don't you want me to go down on you?"

"I don't like it."

"If you can't tell the truth, what are we doing here?"

"I... It's not like that. I just can't get off that way anymore."

"Why?"

"No reason."

"There's a reason."

She exhales, a reticent growl in her throat. "There was... this one guy didn't like it."

"Some guys don't. They're called losers."

"It wasn't his fault, I... kind of surprised him."

I smile. "You're a squirter."

Her face went immediately red, and she looked almost angry. "Maybe. Sometimes."

"Who was he?"

She sipped her coffee and turned her head away. "Just an ex."

"An asshole, you mean."

She shrugged. "He was alright. It didn't really start happening until a few years ago. Usually, it only happens when my... um... climax is especially strong. Intercourse doesn't get me that worked up, so I can avoid it."

"So, your ex was going down on you when you squirted for the first time, and he had a bad reaction."

"It was fucking awful. He thought I peed in his mouth. For that matter, so did I."

Shrugging I say, "Even if you did, piss is sterile."

Cheeks and neck suddenly rosy, she pushed her hair behind her ear. "I don't know why I'm telling you this."

"You're telling me because if the rest of the interview goes well," and I raise my voice a bit, "I'm going to tie you up and fuck you in the ass."

I hear a gasp from a table a few feet away, and a mousy woman is grabbing the cross hanging from her neck, scowling at us.

"Sorry," I said loudly to the woman, "I don't do doubles. Not since the incident."

At this, my companion burst out laughing, and I smiled at her while our prudish neighbor relocated.

"Squirt or don't. Let your body do what it's going to do. That is, so long as you follow my instructions."

She grinned and sipped her coffee.

x x x

Her pussy lips are swollen and fully petalled, and I try not to spend too much time with my tongue in her slit. I simply can't get enough of her taste, but her lengthening moans and bucking hips are incentive enough to keep working her clit. Not to mention the amount of lubricant she's producing. A mixture of my saliva and her milky secretions are pooling in her asshole before dripping to the mat, and I use this fluid to lubricate the fingertip I push into her dirty tunnel.

Back arching, what little it can in her current position, she opens her mouth to let out a rather constant "unnnnnggggggg". I don't push my fingertip beyond the outer sphincter yet - I want her to enjoy easier, low-pressure anal stimulation for a bit. It will make the transition to opening her much more pleasant.

I can tell she's getting close. Her breathing and moaning has taken on a consistent rhythm and tempo. I wipe fresh precum from my cock and smear it into her anus while I increase the pressure and slightly widen the circles my tongue makes around her clit.

Her throat constricts suddenly. "I'm... I'm gonna'... fuck, I..."

I slide a new finger into her cunt and push upward on the ridges I find along her g-spot. "Let it out. Cum for me."

"I... I can't..."

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